Chlorosuccinimide → HCID 22038099, compound

HRID 1790474Notes

Reaction equation

HRID 1790474 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:33]=[CH:32][C:13]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([NH2:31])[CH:29]=4)[CH2:24][CH2:23]3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1>C(#N)C>[F:9][C:10]1[CH:33]=[CH:32][C:13]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([N:22]3[C:30]4[C:25](=[CH:26][C:27]([Cl:1])=[C:28]([NH2:31])[CH:29]=4)[CH2:24][CH2:23]3)[CH2:20][CH2:21]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 22037919HCID 22037919, compound

Product 1

HCID 22038099HCID 22038099, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Chlorosuccinimide (0.24 g) was added at room temperature to a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminoindoline (0.5 g) in acetonitrile (50 ml) and the resultant mixture was stirred for 1 hr. Then the reaction mixture was filtered and concentrated under reduced pressure. Next, a 5 N aqueous solution of sodium hydroxide and ethyl acetate were added thereto and the layers were separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The resulting residue was purified by silica gel column chromatography (methylene chloride/ethanol system) to give the title compound (0.19 g) as a brown oil (yield: 34%).

Workup

  1. filtrationThen the reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. additionNext, a 5 N aqueous solution of sodium hydroxide and ethyl acetate were added
  4. customthe layers were separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/ethanol system)

Sources & evidence

ORD record
ord-91568a1f09ec49e28d81837910dbdcf9
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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